


The Boss's Orders

by CrazyEd



Series: Sub Club [2]
Category: Original Work
Genre: BDSM, Ball Gags, Blindfolds, Boss/Employee Relationship, F/M, First Time Bottoming, Height Differences, Impact Play, Leather, Lingerie, Maledom/Femsub, Masks, Masochism, Orgasms, Play Party, Porn With Plot, St. Andrew's Cross, Suit Kink
Language: English
Status: Completed
Published: 2021-02-13
Updated: 2021-02-13
Packaged: 2021-03-12 20:53:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,342
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29390820
Author URL: https://archiveofourown.org/users/CrazyEd/pseuds/CrazyEd
Summary: A young woman runs into her handsome boss (that she's crushed on for years) in just about the worst place imaginable: Her first BDSM play party. But it's far from his first, and he wants to teach her how to play.A standalone story.
Relationships: Bruno Spadavecchia/Stella Lindberg, Bruno Spadavecchia/Viviana Flores
Series: Sub Club [2]
Series URL: https://archiveofourown.org/series/2159634
Kudos: 8





	1. Chapter 1

Of all the possible situations that Stella could have ran into her boss that she'd had a crush on for years, "while wearing nothing but black cat half-mask and matching lingerie at her first real BDSM play party" was probably the absolute last one she would have wanted. But there he was, dressed in an obsidian black double-breasted suit, flogging the breasts and thighs of a woman chained to a St. Andrew's Cross. She almost called out his name, from pure shock, but restrained herself. Many people at this party, herself included, went by pseudonyms to avoid connecting their private lives to the BDSM scene. She edged closer to the small group of people assembled to watch their scene.

But for her black collar, the woman was dressed entirely in red. She was attached to the cross by red cuffs and the buckles covering her thigh-high platform heel boots. A red eye mask completely covered the upper half of her face, and between her cherry red lips was a massive red ball gag that made her look like she had a small apple in her mouth. To conform to the party rules, she wore red panties and heart-shaped pasties over her otherwise bare breasts. Even her hair was dyed a bright red.

Stella rubbed the side of her mouth. It hurt her jaw just to look at that gag. She couldn't imagine what it must have felt like to wear it. But she had no trouble imagining the tall, slender man turning his flogger on her. Stella flinched every time the lashes of the flogger made contact with the woman's skin, but the woman took each strike with the utmost of elegance. Every sound she made was of pleasure, without the slightest hint of pain, as if he was caressing her with his fingers and not long tails of soft leather. As hard as he was going, Stella would have been screaming for mercy in her shoes (or boots, as it were), but the red-haired woman was nothing but poise out of respect for the people playing around her.

Even from a distance, even behind the mask and gag, it was obvious to Stella how much she was enjoying herself. Stella wanted that for herself. She wanted _him_ for herself, more than ever. And she wanted to know who that woman was. Was she just another guest, playing with him for a few minutes on this one night? Was she his girlfriend? He'd never mentioned a girlfriend at work, but that didn't really say much one way or the other. His wife? Stella highly doubted that, at least; he wore no ring, and his sister would've probably told her if he'd ever gotten married. They were friends, and she was the one who got her the job at her family's auto dealership in the first place.

The last hit was the hardest, a wide sweeping slash across both her breasts, with such force that he spun entirely around to face the crowd. Only then did the woman scream, her high voice muffled by her huge ball gag. He held his hands up in the air, holding the flogger like a gladiator holding his sword to salute the Emperor of Rome. He took a deep bow, as if he was the lead actor of a Broadway play.

Stella watched him stash the flogger inside his suit jacket, undo the boot's buckles and cuffs from the St. Andrew's Cross, and re-cuff her hands together. She remained at attention as he reached into his pocket and slowly withdrew a long delicate chain collar. With a loud snap that made Stella flinch just as hard as the sound of leather on skin did a minute earlier, he attached the collar. Tugging down on it, he forced the woman to bow as well, and then lead her away from the cross.

Stella could hardly believe what she had just witnessed. It was just too much to process. She just watched her boss, who she harbored a massive crush on for _years_ , flog a nearly nude woman. She _had_ to make sure her eyes weren't deceiving her. She walked past the cross, ignoring the next couple set to use it, and followed them. Weaving her way through the crowd, she found them in the social area next to the refreshments bar. He was sitting on a couch, with one hand around his partner's waist, and the other clutching a glass of what looked like whiskey (but was probably just iced tea).

Hesitantly, Stella approached the couple. Up close, there was no doubt in her mind that his man was her boss. Three large jagged scars ran in parallel almost horizontally across his left cheek; a remnant from a car crash nearly a decade ago. There were many swarthy Italian-American men in her area, but only one had those scars. 

Her boss took a sip of his drink. "Hello there," he said to her, pleasantly enough. "Enjoying the party?" Stella jumped. He'd noticed her. She hadn't expected to actually talk to him, but now she had no choice. She couldn't very well just turn around and run away, could she? He'd think she was weird, and even if he didn't actually realize it was _her_ , that was the last thing she wanted.

"He-hello," she said, feeling a bit tongue tied. The woman's head turned to face the direction of the sound, but still wearing the large eye mask, there was no way she could actually see Stella. "Um, yes. That was, um, very impressive. What you just did. Both of you." A sudden thought popped into her head: _'Can he recognize my voice?'_

"Thank you," he said, quite casually, as if she'd merely complemented him on his clothes or new hair cut. His partner mumbled something unintelligible from behind the gag. "From both of us," he added, chuckling, with a nod to his partner. "Care to take a seat?" Stella sat down next to him, as if suddenly magnetized to the couch, staring at her hands on her stockings. "I like your mask. Very pretty," he said.

"Th-thanks," Stella mumbled. Despite (or, perhaps, because of) the lingerie, Stella felt naked next to him.

"First time?" he asked her. She nodded again. "It can be pretty intimidating, your first time. Do you have a name? People call me Scarface. Really original, huh?" She couldn't say the name didn't suit him. Right now, he looked more like a stereotypical mobster than she'd ever seen him, which was saying something. All he was missing was the fedora and Tommy gun.

"Mory," Stella replied. "Mory's fine."

"Well, Mory," "Scarface" replied, unhooking his arm from the woman and setting down his drink in her hand like she was no more than an end table. "Is there something you wanted to say to me?" he asked politely. "Or Josie?" He nodded again, to the bound and gagged woman.

Stella searched for something she'd like to say that she'd also want them to hear. "I... like her boots. They're nice." Josie swung her leg over Scarface's lap, presenting one of the boots for Stella to get a better look. The heels were not _extremely_ tall, only four or five inches at most, but they were thick and wide, with a vulcanized rubber sole and deeply cut treads. The boots had a very heavy and sturdy look, like even if she tripped they would hold up her body _for_ her. Next to Stella's chunky-heeled mary janes, which was the best she could find in her closet for shoes that matched her (lack of) an outfit, they looked like plate armour.

"I like them too," Scarface admitted. "Short women can be so hard to kiss. Platform heels really help, when you're as tall as me." He stroked Josie's chin. "Isn't that right?" He removed the gag from her mouth and let it hang around her neck like a second collar. With only the slightest bit of difficulty, she unlatched the wrist cuffs herself, and took off the eye mask.

"That's never stopped you from dating short women," she replied, in a haughty tone that surprised Stella. It was as if she had not been strapped up to the wall, her body and her pain on display for all to ogle, minutes before. Josie took a good look at Stella, and said, "She wouldn't need heels, Don. She'd need stilts." She dropped the mask into Scarface's jacket pocket.

Underneath her mask, Stella blushed. She knew all too well about the seventeen inch difference between her and her boss. Every day, at work, she was forced to crane her neck up to look him in the eye. Even standing on her tip-toes, she wasn't tall enough to kiss him. She wasn't even _close_.

Scarface turned towards Josie, and clapped her on the thigh. "Who said anything about kissing? We're just talking." He looked back at Stella. "Right?" She nodded furiously.

"Yes, sir," she said automatically.

Josie smiled at her politely. "It's bad manners to use titles without permission," she told Stella.

"Right," Stella said, nodding. All the first timer guides she had read said that exact same thing. "My bad."

"Newbie mistake," she said, waving Stella off, reclined back into the couch, and took a sip from Scarface's drink still in her hand. With her leg still swung over Scarface's leg, her own legs were spread quite widely, giving Stella a good view of her red panties. She did not seem embarrassed in the slightest, but Stella certainly was.

Scarface chuckled. "Perhaps I should punish you for that mistake, so you'd never make it again." He leaned in close, and whispered into her ear, "Would you like that, _Stella_?"

She gasped. He knew it was her. _Oh god, he knew it was her_. She turned to him, and immediately whispered back, "How did you know?"

Bruno chuckled. "How could I not? How many times do I have to tell you that you don't have to call me 'sir'?"

Stella went scarlet. Of all the stupid reasons it could've possibly been, it had to be that one. She felt like the punchline of a bad joke about naughty secretaries. He stood up, lording over her from seemingly a mile away, one hand casually swirling the ice around his drink, the other extended to her. "You never answered my question," he said. Stella looked up at him, dazed. "Would you like that?"

She reached up, and put her hand in his. His fingers engulfed her tiny hand, surrounding her in a cocoon of gentle warmth. Bruno drained the last of his drink and gave the cup to Josie. "This won't take long," her told her, and whisked Stella back to the play area. She didn't know what to expect next, but whatever it was, she hoped she'd be able to look him in the eye come Monday morning.


	2. Chapter 2

"Is this really okay?" Stella asked. "Your girlfriend..."

"We came here together, and we're together, but we're not, like, _together_ together," said Bruno. But Scarface added, "A slave doesn't get to dictate who her master plays with. Don't worry about Josie."

Bruno lead her by the hand to what appeared to be a pommel horse, except it lacked pommels, and helped her onto it. She had to awkwardly crane her leg over it, spreading her legs entirely, and once straddling it, she found her legs too short to reach the floor. It was like riding an actual horse without stirrups. No stirrups, but a very smooth, plush leather saddle that she sank into easily. He took her hands and walked in front of the spanking horse, and slowly pulled her forward, stretching her out on top of it.

She watched him remove the eye mask from his pocket. With a deft hand, he quickly swapped it out her cat half-mask. Bruno placed a hand on her head and stroked her as he walked from one end of the horse to the other, brushing his hand all the way from the top of her head to her garter belt. Stella shifted atop the horse, enjoying the sensation of the cool leather against her bare skin.

He dropped the tails of the flogger onto her skin. "I am going to strike you for calling me 'sir' without permission. You are to count each strike out loud. We will start with five." Scarface brushed her bare skin like a painter on a fresh canvas. The tails danced up and down her back, sending shivers down her spine. "Do you understand?"

Stella swallowed. "Yes."

He moved the tails to her thighs, brushing upwards, from the back of her knee, over the curve of her rear, and pooling on her tailbone. "If at any point you can not handle your punishment, I am to know immediately. Merely telling me 'Stop' will suffice." He repeated the process on her other leg. Stella pushed her hips away from the source of the tingling, inadvertently rubbing the front of her body against the horse. "Do you understand?"

"Yes," Stella gasped.

He struck as soon as she answered, landing the tails horizontally across the meatiest part of her ass. Stella yelped, more out of surprise than pain. He definitely had stopped just dangling the flogger above her, but she could not say that it had really _hurt_. She had expected a sting, but only received a pleasant thump. "One," Stella murmured, burying her cheek against the leather saddle.

"Louder, or I won't be able to hear you," said Scarface. The next hit came much harder. She felt it even after the leather left her skin, but it would still be hard to say it hurt, per se. Josie had endured far worse than that, and maintained her composure. Stella endeavored to do the same. If it was just this much, she could handle it.

"Two," she said, matter-of-factly, enunciating the word clearly for him. Perhaps he took that as a challenge to his authority, because the next lashing came down much faster upon her ass. Stella's back arced, raising her head, and she yelped again; this time, it _was_ pain. The thump had finally become a sting, like the sensation she first felt when trying out a cheap flogger she'd bought online on her own thighs.

"Three," she said, resting her head back down on the saddle. "Three," she repeated, to herself. Only two more to go. She could handle two more.

"Four," she grunted, enduring the pain of the next sting of the leather. "Five," she gasped, as the final one impacted against her flesh. "That's five."

"Yes, it is," agreed Scarface. "You did very well. But your punishment is not over. You will count out five more. Do you understand?"

"Yes." This time, he flogged her thighs, an underhanded strike that impacted against the bottom of her thigh, and lanced upwards towards her ass. "One," she said, growing more confident in herself. It hurt, true, but she could start to feel the warmth spreading throughout her lower body. The next lashing was the same, only on her opposite side. "Two."

Three and Four were a repeat of One and Two, two hard hits to either thigh one after the other. "Five," Stella squeaked, surprised by the blow landing square on her ass once more.

Scarface patted her ass with the flat of his palm. "That's ten," he said, softly caressing her increasingly tender flesh. "This time, you will receive ten, and then your punishment will be complete. Do you understand?"

"Yes."

Stella tried. She really did. There was pain, but there was something charged about it. It wasn't pain meant to hurt her. The mere knowledge of why it was happening to her, that she had willingly volunteered to suffer it as punishment for her mistakes, excited her almost as much as the pain itself. But each blow raining down on her began to pile up on the last. Despite Scarface varying his target at seemingly random, and never going any farther in intensity after that third hit, he started to wear her down.

Cheeks burning (both on her face and her ass), she cried out in ecstasy on the seventh hit, her seventeenth overall. Her back arced, and her hips bucked, grinding her crotch straight into the padded leather of the spanking horse. Her legs quivered as a wave of something else, not pain or the warmth of blood rushing to the surface just underneath her skin, poured over her body. Scarface had to catch her by the shoulders to keep from sliding right off the horse. In the embrace of his arms, Stella leaned her cheek against his chest, breathless.

"I think you had enough," suggested Bruno. "Did you really just come?" he asked. Stella nodded, rubbing her cheek against the high quality black fabric of his suit. "Let's put a rain check on those last three hits, huh?"

Stella nodded again. "Sorry," she said, as he slowly helped her off the spanking horse and onto shaky feet. "I couldn't manage to the end." Freed from his arms, she felt the growing embarrassment of having just came in front of her first crush, and current boss. But even that just excited her more and more. What truly embarrassed her was the shame of not being able to finish the scene.

"Never be sorry for stopping a scene, with me, or anyone else," said Bruno, protectively. "You did very well, especially for a first-timer."

"Thanks," she said, smiling up at the sound of his voice. A moment later, the eye mask slipped off the top of her head and her own mask was replaced. She could see Bruno again, and for the first time, wondered what the exchange made him feel. "Did _you_ have fun?" she asked, curious.

"You did very well," Bruno repeated. "Flogging you was quite... _interesting_ , let's say. I was certainly entertained." He grasped her by the upper arms and said, "Why don't you just relax for a moment while I clean this up?"

Stella nodded, had a realization, and then blushed. By "clean up", he probably meant the results of her orgasm. She turned around, not wanting to see how much of a mess she made on the horse, and found a convenient wall to rest her weary body on. She slid down the wall and turned to watch Bruno wiping down the horse. He focused most of his attention on making sure the horse was clean for it's next user, but every so often he would look directly at Stella and smile warmly at him. Stella smiled back and lifted a hand to show she'd noticed his glance over to her.

Once the horse was satisfactorily cleaned, Bruno walked over to her, bent down, and scooped her up in his arms. Stella yelped again. He chuckled and said, "You're even lighter than I thought you'd be." Stella said nothing, but rested her head against his chest. He princess-carried her though the party, and only set her down once they reached the social area. Stella wrapped her arm around his for support, and both looked for Josie.

But she was nowhere to be seen. Stella wondered if she had gotten bored of waiting for Bruno and wandered off to find someone else to play with, or if she'd left the party entirely. Was she actually upset that he had abandoned her to go play with another woman? Stella looked up at Bruno, wondering what he thought of the situation. To her surprise, he didn't seem very concerned. "She probably just went back to our hotel room or something."

Stella clung tighter to his arm, pulling him tight against her breasts. "Maybe... we should go up to your room, and look for her?"

It took Bruno a moment to realize what she was suggesting, but when he did he smiled from ear to ear, absolutely melting Stella. She thought her legs might fall out right from under her. If only she had Josie's boots. "We probably should."

**Notes for the Chapter:**

> In reality, you'd want to negotiate the rules and terms of the scene _before_ starting _anything_ , which is why this is erotic fiction instead of a how-to flog someone guide.


End file.
